US9882146B2 - Heterocyclic compound and organic electronic element containing same - Google Patents

Heterocyclic compound and organic electronic element containing same Download PDF

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US9882146B2
US9882146B2 US15/087,847 US201615087847A US9882146B2 US 9882146 B2 US9882146 B2 US 9882146B2 US 201615087847 A US201615087847 A US 201615087847A US 9882146 B2 US9882146 B2 US 9882146B2
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compound
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US20160218298A1 (en
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Sangbin Lee
Dong Hoon Lee
Hoyong Lee
Kongkyeom Kim
Jungi Jang
Sung Kil Hong
Changhwan Shin
Hyungjin Lee
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LG Chem Ltd
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LG Chem Ltd
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Assigned to LG CHEM, LTD. reassignment LG CHEM, LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HONG, SUNG KIL, JANG, Jungi, KIM, Kongkyeom, LEE, DONG HOON, LEE, HOYONG, LEE, HYUNGJIN, LEE, Sangbin, SHIN, Changhwan
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    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present disclosure relates to a novel heterocyclic compound and to an organic electronic device comprising the same.
  • organic electronic device refers to a device that requires the exchange of an electronic charge between an electrode and an organic material using holes and/or electrons.
  • the organic electronic device can be largely classified according to its operational principle into two types as follows.
  • One type is an electronic device having a configuration in which an exciton is formed in an organic material layer by the entry of photons into the device from an external light source, and is then separated into an electron and a hole, which are transferred to different electrodes as a current source (voltage source), and the other type is an electric device having a configuration in which a voltage or a current is applied to two or more electrodes to inject a hole and/or an electron into an organic semiconductor positioned at the interface between the electrodes, and the device is operated using the injected electron and hole.
  • Examples of the organic electronic device include an organic light-emitting device, an organic solar cell, an organic transistor and the like, all of which require a hole-injecting or hole-transporting material, an electron-injecting or electron-transporting material or a light emitting material to drive the device.
  • the organic light-emitting device will be mainly and specifically described, but in the above-mentioned organic electronic devices, the hole-injecting or hole-transporting material, the electron-injecting or electron-transporting material, or the light-emitting material injection functions according to a similar principle.
  • the term “organic light-emitting phenomenon” refers to a phenomenon in which electric energy is converted to light energy using an organic material.
  • the organic light-emitting device that uses the organic light-emitting phenomenon usually has a structure comprising an anode, a cathode and an organic material layer interposed therebetween.
  • the organic layer often has a multilayer structure consisting of a plurality of layers made of different materials in order to increase the efficiency and stability of the organic light-emitting device.
  • the organic material layer may consist of a hole-injecting layer, a hole-transporting layer, a light-emitting layer, an electron-transporting layer, an electron-injecting layer and the like.
  • the organic-light emitting device having this structure, when a voltage is applied between two electrodes, holes from the anode and electrons from the cathode are injected into the organic material layer, and the injected holes and electrons are combined with each other to form excitons. When the excitons subsequently drop to the ground state, light is emitted.
  • heterocyclic compound having a chemical structure which, depending on the substituent groups thereof, may provide various functions required for an organic electronic device, and to provide an organic electronic device comprising the same.
  • the present disclosure also provides an organic electronic device comprising a first electrode, a second electrode and one or more organic material layers interposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprise the heterocyclic compound of formula 1.
  • novel compound according to the present invention may be used as a material for the organic material layer of organic electronic devices, including organic light-emitting devices.
  • the use of the novel compound according to the present invention makes it possible to improve the efficiency of organic electronic devices including organic light-emitting devices, lower the driving voltage of the devices, and/or increase the lifetime of the devices.
  • FIG. 1 shows an example of an organic light-emitting device consisting of a substrate 1 , an anode 2 , a light-emitting layer 3 and a cathode 4 .
  • FIG. 2 shows an example of an organic light-emitting device consisting of a substrate 1 , an anode 2 , a hole-injecting layer 5 , a hole-transporting layer 6 , a light-emitting layer 7 , an electron-transporting layer 8 and a cathode 4 .
  • the present disclosure provides the compound represented by formula 1.
  • examples of the trivalent heteroatom include, but are not limited to, N and P.
  • the trivalent heteroatom is N.
  • X 1 to X 3 are the same or different, and are each independently N or CH, and at least one of X 1 to X 3 is N.
  • n is 2.
  • X 1 to X 3 , Ar 1 to Ar 3 and L may be the same or different.
  • Ar 3 is selected from among the following structures:
  • a, c, d and e are each an integer ranging from 1 to 6,
  • “ ” means a portion linked to another substituent group.
  • it may be linked to a heterocyclic ring containing X 1 to X 3 , when L is a direct bond.
  • Ar 1 and Ar 2 are the same or different, and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted pyridine group.
  • L is a direct bond or a substituted or unsubstituted phenylene group.
  • the alkyl group may be linear or branched, and the number of carbon atoms thereof is not specifically limited, but preferably ranges from 1-50.
  • Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl and heptyl groups.
  • the alkenyl group may be linear or branched, and the number of carbon atoms thereof is not specifically limited, but preferably ranges from 2-50.
  • Specific examples of the alkenyl group include, but are not limited to, aryl-substituted alkenyl groups such as stylbenyl and styrenyl groups.
  • the alkoxy group may be linear or branched, and the number of carbon atoms thereof is not specifically limited, but preferably ranges from 1-50.
  • the lengths of the alkyl, alkenyl and alkoxy groups in the compound do not influence the conjugation length of the compound, but merely influence the method used to apply the compound to an organic electronic device, for example, a vacuum deposition method or a solution application method, and thus the numbers of carbon atoms of these groups are not specifically limited.
  • the cycloalkyl group is not specifically limited, but preferably contains 3-60 carbon atoms.
  • Preferred examples of the cycloalkyl group include cyclopentyl and cyclohexyl groups.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the fluorenyl group has a structure in which two cyclic organic compounds are linked to each other by one atom, and examples thereof include
  • the fluorenyl groups include an open fluorenyl group having a structure in which one of two cyclic compounds linked to each other by one atom is broken.
  • Examples of the open fluorenyl group include
  • the number of carbon atoms of the amine group is not specifically limited, but preferably ranges from 1-50.
  • Specific examples of the amine group include, but are not limited to, methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl-anthracenylamine, diphenylamine, phenylnapthylamine, ditolylamine, phenyltolylamine and triphenylamine groups.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group or a substituted or unsubstituted triarylamine group.
  • the aryl group of the arylamine group may be a monocyclic or polycyclic aryl group.
  • the arylamine group containing two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or both the monocyclic aryl group and the polycyclic aryl group.
  • arylamine group examples include, but are not limited phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methyl-phenylamine, 4-methyl-naphthylamine, 2-methyl-biphenylamine, 9-methyl-anthracenylamine, diphenlamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, carbazole and triphenylamine groups.
  • the number of carbon atoms of each of the aryloxy, arylthioxy, arylsulfoxy and aralkylamine groups is not specifically limited, but preferably ranges from 6-50.
  • the aryl group of each of the aryloxy, arylthioxy, arylsulfoxy and aralkylamine groups is as defined above.
  • alkyl group of each of the alkylthioxy, alkylsulfoxy, alkylamine and aralkylamine groups is as defined above.
  • heteroaryl group of the heteroarylamine group may be selected from the above-described examples of the heterocyclic group.
  • the arylene, alkenylene, fluorenylene and heteroarylene groups are divalent aryl, alkenyl, fluorenyl and heteroaryl groups, respectively. These groups are as defined above for the aryl, alkenyl, fluorenyl and heteroaryl groups, except that they are divalent groups.
  • substituted or unsubstituted means that it is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, a silyl; group, an arylalkenyl group, an aryl group, an aryloxy group, an alkylthioxy group, an alkylsulfoxy group, an arylsulfoxy group, a boron group, an alkylamine group, an aralkylamine group, an arylamine group, a heteroaryl group, a carbazole group, an arylamine group, a fluorenyl group, a nitrile group, a nitro group, a hydroxyl group, a cyano group and a heterocyclic group containing at least one heteroatom selected from among N, O,
  • the present disclosure provides a novel heterocyclic compound represented by formula 1 above.
  • This compound may be used for an organic material layer in an organic electronic device due to its structural specificity.
  • Ar 3 is a substituted or unsubstituted 2,7-naphthyl group, a substituted or unsubstituted 1,8-naphthyl group, a substituted or unsubstituted 1,6-naphthyl group, a substituted or unsubstituted 1,7-naphthyl group, or a substituted or unsubstituted 3,6-fluorenyl group.
  • Ar 3 is a 2,7-naphthyl group.
  • Ar 3 is a 1,8-naphthyl group.
  • Ar 3 is a 1,7-naphthyl group.
  • Ar 3 is a 1,6-naphthyl group.
  • Ar 3 is a 3,6-fluorenyl group.
  • the effect of the compound as an electron donor can be further increased to increase the efficiency with which an electron is transported to and injected into a light-emitting layer. For this reason, the compound may have excellent characteristics in terms of voltage and efficiency.
  • Ar 3 is a 2,7-naphthyl group substituted with an aryl group.
  • Ar 3 is a 2,7-naphthyl group substituted with a phenyl group.
  • Ar 3 is a 1,8-naphthyl group substituted with an aryl group.
  • Ar 3 is a 1,8-naphthyl group substituted with a phenyl group.
  • Ar 3 is a 1,7-naphthyl group substituted with an aryl group.
  • Ar 3 is a 1,7-naphthyl group substituted with a phenyl group.
  • Ar 3 is a 1,6-naphthyl group substituted with an aryl group.
  • Ar 3 is a 1,6-naphthyl group substituted with a phenyl group.
  • the compound represented by formula 1 is represented by any one of the following formulas 1-a, 1-b, 1-c, 1-d and 1-e:
  • At least one of X 1 to X 3 in formula 1 may be a trivalent heteroatom.
  • At least one of X 1 to X 3 may be N or P.
  • X 1 to X 3 may all be N.
  • X 1 may be N, and X 2 and X 3 may be CH.
  • X 2 may be N, and X 1 and X 3 may be CH.
  • X 3 may be N, and X 1 and X 2 may be CH.
  • X 1 and X 2 may be N.
  • X 3 is CH.
  • X 1 and X 3 may be N.
  • X 2 is CH.
  • X 2 and X 3 may be N.
  • X 1 is CH.
  • n in formula 1 when n in formula 1 is 2, the structures linked to Ar 3 may be the same or different.
  • Ar 1 and Ar 2 in formula 1 may be substituted or unsubstituted aryl or heteroaryl groups.
  • Ar 1 and Ar 2 may be the same or different, and may be each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridyl group or a substituted or unsubstituted naphthyl group.
  • Ar 1 and Ar 2 are the same or different, and may be each independently an alkyl-substituted phenyl group, an alkoxy-substituted phenyl group, a halogen-substituted phenyl group or a trifluoro-substituted phenyl group.
  • Ar 1 and Ar 2 are the same or different, and may be each independently an alkyl-substituted biphenyl group, an alkoxy-substituted biphenyl group, a halogen-substituted biphenyl group or a trifluoro-substituted biphenyl group.
  • Ar 1 and Ar 2 are the same or different, and may be each independently an alkyl-substituted pyridyl group, an alkoxy-substituted pyridyl group, a halogen-substituted pyridyl group or a trifluoro-substituted pyridyl group.
  • Ar 1 and Ar 2 are the same or different, and may be each independently an alkyl-substituted phenyl group, an alkoxy-substituted naphthyl group, a halogen-substituted naphthyl group or a trifluoro-substituted naphthyl group.
  • Ar 1 and Ar 2 are the same or different, and may be each independently a methyl-substituted phenyl group, a methoxy-substituted phenyl group, a fluoro-substituted phenyl group or a trifluoro-substituted phenyl group.
  • Ar 1 and Ar 2 are the same or different, and may be each independently
  • R 0 may be selected from the group consisting of alkyl, alkoxy, halogen and trifluoro groups.
  • Ar 1 and Ar 2 are the same or different, and may be each independently a methyl-substituted biphenyl group, a methoxy-substituted biphenyl group, a fluoro-substituted biphenyl group or a trifluoro-substituted biphenyl group.
  • Ar 1 and Ar 2 are the same or different, and may be each independently a methyl-substituted pyridyl group, a methoxy-substituted pyridyl group, a fluoro-substituted pyridyl group or a trifluoro-substituted pyridyl group.
  • Ar 1 and Ar 2 are the same or different, and may be each independently a methyl-substituted naphthyl group, a methoxy-substituted naphthyl group, a fluoro-substituted naphthyl group or a trifluoro-substituted naphthyl group.
  • Ar 1 and Ar 2 are the same or different and may be each independently a phenyl, biphenyl, pyridyl or naphthyl group.
  • Ar 1 and Ar 2 are the same or different, and may be each independently
  • Ar 1 and Ar 2 are the same or different, and may be each independently
  • Ar 1 and Ar 2 are the same or different, and may be each independently
  • Ar 1 and Ar 2 are the same or different, and may be each independently
  • Ar 1 and Ar 2 are the same or different, and may be each independently
  • Ar 1 and Ar 2 are the same or different, and may be each independently
  • L may be a direct bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted alkenylene group, a substituted or unsubstituted fluorenylene group or a substituted or unsubstituted heteroarylene having a heteroatom selected from among O, N, S and P.
  • L may be a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted pyridylene group or a substituted or unsubstituted biphenylene group.
  • L may be a phenylene, naphthalene, fluorenylene, pyridylene or biphenylene group.
  • L may be a direct bond
  • L may be a phenylene group. Specifically, L may be
  • L may be any organic radical
  • L is linked to either the heterocyclic ring including X 1 to X 3 of formula 1 or Ar 3 .
  • the compound represented by formula 1 is any one of the following compounds 1-a-1 to 1-a-16, 2-a-1 to 2-a-11, 3-a-1 to 3-a-4, 1-b-1 to 1-b-16, 2-b-1 to 2-b-11, 3-b-1 to 3-b-4, 1-c-1 to 1-c-16, 2-c-1 to 2-c-11, 3-c-1 to 3-c-4, 1-d-1 to 1-d-16, 2-d-1 to 2-d-11, 3-d-1 to 3-d-4, 1-e-1 to 1-e-10, and 2-e-1 to 2-e-8.
  • the compound represented by formula 1-a is any one of the following compounds 1-a-1 to 1-a-16, 2-a-1 to 2-a-11 and 3-a-1 to 3-a-4:
  • the compound represented by formula 1-b is any one of the following compounds 1-b-1 to 1-b-16, 2-b-1 to 2-b-11 and 3-b-1 to 3-b-4.
  • the compound represented by formula 1-c is any one of the following compounds 1-c-1 to 1-c-16, 2-c-1 to 2-c-11 and 3-c-1 to 3-c-4.
  • the compound represented by formula 1-d is any one of the following compounds 1-d-1 to 1-d-16, 2-d-1 to 2-d-11 and 3-d-1 to 3-d-4:
  • the compound represented by formula 1-e is any one of the following compounds 1-e-1 to 1-e-10 and 2-e-1 to 2-e-8:
  • the compound of formula 1 may have suitable characteristics for use as an organic material layer in an organic electronic device as a result of introducing various substituents into the heterocyclic structure, which is the core structure shown in formula 1.
  • the conjugation length and energy band gap of a compound have a close relationship with each other. Specifically, as the conjugation length of a compound increases, the energy band gap decreases. As described above, the core structure of the compound of formula 1 has a limited conjugation length, and thus has a high energy band gap.
  • compounds having various energy band gaps can be synthesized by introducing various substituents into the positions Ar 1 to Ar 3 and R1 to R6 of the core structure having a high energy band gap as described above. It is generally easy to control the energy band gap by introducing the substituents of a core structure having a high energy band gap. However, when a core structure has a low energy band gap, it is difficult to control the energy band gap so as to have a high level by introducing substituents into the core structure.
  • the HOMO and LUMO energy levels of the compound can also be controlled by introducing various substituents into the positions of Ar 1 to Ar 3 and R1 to R6 of the above-described core structure.
  • a compound having the inherent characteristics of the introduced substituents can be synthesized.
  • substituents which are mainly used in materials for the hole-injecting layer, hole-transporting layer, light-emitting layer and electron-transporting layer of an organic electronic device are introduced into the above-described core structure, a material that satisfies the conditions required for each of the organic material layers can be synthesized.
  • the compound of formula 1 may have a suitable energy level for use as a hole-injecting material and/or a hole-transporting material in an organic light-emitting device.
  • a suitable energy level for use as a hole-injecting material and/or a hole-transporting material in an organic light-emitting device.
  • the device when a compound having a suitable energy level, attributable to the substituents introduced therein, is selected from among the compounds of formula 1 and used in an organic light-emitting device, the device may have a low driving voltage and a high optical efficiency.
  • the energy band gap can be finely controlled, while the characteristics of the interface between organic materials in an organic electron device can be improved and the compound of formula 1 may be used in various applications.
  • the compound of formula 1 has excellent thermal stability due to its high glass transition temperature (T g ). This increase in the thermal stability is an important factor that provides driving stability to a device.
  • the compound of formula 1 can be prepared based on Preparation Examples, which will be described below.
  • the heterocyclic compound of formula 1 can be prepared by substituting the heterocyclic ring of formula 1, which includes X 1 to X 3 , with Ar 1 , Ar 2 and L, and then bonding the two substituted heterocyclic rings, which include X 1 to X 3 , to Ar 3 .
  • the present disclosure also provides an organic electronic device comprising the compound of formula 1.
  • the organic electronic device may have a structure comprising a first electrode, a second electrode and one or more organic material layers interposed between the first and second electrodes.
  • the organic electronic device may be selected from the group consisting of an organic light-emitting device, an organic solar cell and an organic transistor.
  • the organic electronic device may be an organic light-emitting device.
  • an organic light-emitting device comprising a first electrode, a second electrode and one or more organic material layers interposed between the first and second electrodes, wherein one or more of the organic layers comprise the heterocyclic compound represented by formula 1.
  • the organic material layers of the organic light-emitting device according to the present disclosure may have a single-layer structure or a multilayer structure consisting of two or more organic layers.
  • the organic light-emitting device according to the present disclosure may have a structure comprising organic material layers, including a hole-injecting layer, a hole-transporting layer, a light-emitting layer, an electron-transporting layer and an electron-injecting layer.
  • the structure of the organic light-emitting device is not limited thereto, and may comprise a smaller number of organic material layers.
  • the organic material layers of the organic light-emitting device may include one or more of a hole-injecting layer, a hole-transporting layer and a layer that performs both hole injection and hole transport, and one or more of the layers may comprise the compound represented by formula 1.
  • the organic material layers of the organic light-emitting device may include a hole-injecting layer, which may comprise the compound represented by formula 1.
  • the organic material layers of the organic light-emitting device may include a hole-transporting layer, which may comprise the compound represented by formula 1.
  • the organic material layers of the organic light-emitting device may include a hole-transporting layer and a hole-injecting layer, in which the hole-transporting layer and the hole-injecting layer may comprise the compound represented by formula 1.
  • the organic material layers may include a light-emitting layer, in which the light-emitting layer may comprise the compound represented by formula 1.
  • the compound represented by formula 1 may be included as a host in the light-emitting layer.
  • the organic material layer comprising the compound represented by formula 1 may include the compound of formula 1 as a host, and may include another organic compound, a metal or a metal compound as a dopant.
  • the organic material layers may include one or more of an electron-transporting layer, an electron-injecting layer or a layer that performs both electron transport and electron injection, wherein one or more of the layers may comprise the compound represented by formula 1.
  • the organic material layers of the organic light-emitting device may include an electron-injecting layer, wherein the electron-injecting layer may comprise the compound represented by formula 1.
  • the organic material layers of the organic light-emitting device may include an electron-transporting layer, wherein the electron-transporting layer may comprise the compound represented by formula 1.
  • the organic material layers of the organic light-emitting device may include an electron-transporting layer and an electron-injecting layer, wherein the electron-transporting layer and the electron-injecting layer may comprise the compound represented by formula 1.
  • the compound represented by formula 1 may be included in the light-emitting layer, the layer that performs all hole injection, hole transport and light emission, the layer that performs both hole transport and light emission, or the layer that performs both electron transport and light emission.
  • the organic material layers of the organic light-emitting device may include, in addition to the organic material layer comprising the heterocyclic composition represented by formula 1, a hole-injecting layer or a hole-transporting layer, which comprises a compound containing an arylamino group, a carbazole group or a benzcarbazole group.
  • the organic electronic device may be an organic solar cell.
  • an organic solar cell comprising a first electrode, a second electrode and one or more organic material layers, including a photoactive layer, interposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprise the heterocyclic compound represented by formula 1.
  • the organic solar cell may include an electron-transporting layer, wherein the electron-transporting layer may comprise the compound represented by formula 1.
  • the photoactive layer may comprise the compound represented by formula 1.
  • the organic solar cell may include a photoactive layer, an electron donor and an electron acceptor, wherein the photoactive layer, the electron donor and the electron acceptor may comprise the compound represented by formula 1.
  • the organic solar cell when the organic solar cell receives a photon from an external light source, an electron and a hole are generated between the electron donor and the electron acceptor. The generated hole is transported to the anode through the electron donor layer.
  • the organic solar cell may further include an additional organic material layer.
  • the organic solar cell may comprise a material having various functions in order to reduce the number of organic material layers therein.
  • the organic electronic device may be an organic transistor.
  • an organic transistor comprising a source, a drain, a gate and one or more organic material layers.
  • the organic transistor may include a charge-generating layer, wherein the charge-generating layer may comprise the compound represented by formula 1.
  • the organic transistor may include an insulating layer, wherein the insulating layer may be located on a substrate and the gate.
  • the organic material layers may be formed of the same or different materials.
  • the organic electronic device may have the structures shown in FIGS. 1 and 2 , but is not limited thereto.
  • FIG. 1 illustrates an organic electronic device having a structure in which a substrate 1 , an anode 2 , a light-emitting layer 3 and a cathode 4 are sequentially deposited.
  • the compound of formula 1 may be included in the light-emitting layer 3 .
  • FIG. 2 illustrates an organic electronic device having a structure in which a substrate 1 , an anode 2 , a hole-injecting layer 5 , a hole-transporting layer 6 , a light-emitting layer 7 , an electron-transporting layer 8 and a cathode 4 are sequentially deposited.
  • the compound represented by formula 1 may be included in one or more of the hole-injecting layer 5 , the hole-transporting layer 6 , the light-emitting layer 7 and the electron-transporting layer 8 .
  • the organic electronic device according to the present disclosure can be fabricated using the same materials and method as known in the art, except that one or more of the organic material layers may comprise the compound of the present disclosure, that is, the compound of formula 1.
  • the organic electronic device according to the present disclosure can be fabricated by sequentially depositing a first electrode, one or more organic material layers and a second electrode on a substrate.
  • the organic electronic device can be fabricated by depositing a metal, a conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form an anode, forming organic material layers, including a hole-injecting layer, a hole-transporting layer, a light-emitting layer and an electron-transporting layer, on the anode, and then depositing thereon a material that may be used to form a cathode.
  • the organic electronic device may also be fabricated by sequentially depositing a cathode material, one or more organic material layers and an anode material on the substrate.
  • the compound of formula 1 can be formed into an organic material layer using a solution application method in addition to the physical vacuum deposition method.
  • solution application method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating or the like, but is not limited thereto.
  • the organic electronic device can also be fabricated by sequentially depositing a cathode material, organic material layers and an anode material on a substrate (International Patent Application Publication No. WO 2003/012890).
  • the fabrication method is not limited to the above methods.
  • the anode material is preferably a material having a high work function, so that holes can be easily injected into the organic material layers.
  • an anode material that may be used in the present invention include, but are not limited to, metals such as vanadium, chromium, copper, zinc or gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) or indium zinc oxide (IZO); metal/oxide combinations such as ZnO: Al or SNO 2 : Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline.
  • metals such as vanadium, chromium, copper, zinc or gold, or alloys thereof
  • metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) or indium zinc oxide (IZO)
  • metal/oxide combinations such as ZnO: Al or S
  • the cathode material is preferably a material having a low work function, so that electrons are easily injected into the organic material layers.
  • Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and multilayer materials such as LiF/Al or LiO 2 /Al.
  • the hole-injecting material is a material that can easily receive holes from the anode at a low voltage, and the HOMO (highest occupied molecular orbital) of the hole-injecting material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layers.
  • the hole-injecting material include, but are not limited to, metal porphyrin, oligothdophene, and arylamine-based organic materials, hexanitrile hexaazatriphenyiene and quinacridone-based organic materials, perylene-based organic materials, anthraquinone, polyandline-based or polythiophene-based conductive polymers and the like.
  • the hole-transporting material is preferably a material having high hole mobility, which is capable of transferring holes from the anode or the hole-injecting layer to the light-emitting layer.
  • Specific examples of the hole-transporting material include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated portions and non-conjugated portions.
  • the light-emitting material a material capable of emitting visible light, by receiving holes and electrons from the hole-transporting layer and from the electron-transporting layer and combining the received holes and electrons, and is preferably a material having high quantum efficiency for fluorescence and phosphorescence.
  • the light emitting material include, but are not limited to, an 8-hydroxyquinoline aluminum complex (Alg 3 ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole-, benzthiazole- and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; and compounds such as polyfluorene and rubrene.
  • Alg 3 8-hydroxyquinoline aluminum complex
  • carbazole-based compounds dimerized styryl compounds
  • BAlq 10-hydroxybenzoquinoline-metal compounds
  • benzoxazole-, benzthiazole- and benzimidazole-based compounds benzoxazole-, benzthiazole- and benzimidazole-based compounds
  • PV poly(p-phenylenevinylene)-based polymers
  • spiro compounds and compounds such as polyfluorene and rubren
  • the electron-transporting material is a material that can easily receive electrons from the cathode and transfer the received electrons to the light-emitting layer. It is preferably a material having high electron mobility. Specific examples of the electron-transporting material include, but are not limited to, a 8-hydroxyquinoline aluminum complex; complexes including Alg 3 ; organic radical compounds; and hydroxyflavone-metal complexes.
  • the organic electronic device may be a front side light-emitting type, a rear side light-emitting type or a both-side light-emitting type, depending on the material used.
  • Compound 3-A was prepared in the same manner as compound 1-B, except that 4-chloro-2,6-diphenylpyrimidine was used instead of compound 1-A.
  • Compound 3-B was prepared in the same manner as compound 1-C, except that compound 3-A was used instead of compound 1-B.
  • Compound 2-a-1 was prepared in the same manner as compound 1-a-1, except that compound 3-B was used instead of compound 1-C.
  • Compound 4-A was prepared in the same manner as compound 1-B, except that 3-chloro-2,6-diphenylpyrimidine was used instead of compound 1-A.
  • Compound 4-B was prepared in the same manner as compound 1-C, except that compound 4-A was used instead of compound 1-B.
  • Compound 2-a-8 was prepared in the same manner as compound 1-a-1, except that compound 4-B was used instead of compound 1-C.
  • Compound 1-b-1 was prepared in the same manner as compound 1-a-1, except that 1,8-dibromonaphthalene was used instead of 2,7-dibromonaphthalene.
  • Compound 1-c-1 was prepared in the same manner as compound 1-a-1, except that 1,6-dibromonaphthalene was used instead of 2,7-dibromonaphthalene.
  • Compound 1-d-1 was prepared in the same manner as compound 1-a-1, except that 1,7-dibromonaphthalene was used instead of 2,7-dibromonaphthalene.
  • Compound 1-e-1 was prepared in the same manner as compound 1-a-1, except that 3,6-dibromo-9,9-dimethyl-9H-fluorene was used instead of 2,7-dibromonaphthalene.
  • a glass substrate having ITO (indium tin oxide) coated thereon to a thickness of 1,000 ⁇ was placed in distilled water containing a detergent dissolved therein, and was ultrasonically washed.
  • the detergent was a product manufactured by Fischer Co., and the distilled water was distilled water filtered twice through a filter (Millipore Co.). After the ITO has been washed for 30 minutes, it was ultrasonically washed twice with distilled water for 10 minutes. After the completion of washing with distilled water, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, methanol or the like, and was dried, after which it was transported to a plasma cleaner. Then, the substrate was cleaned with oxygen plasma for 5 minutes, and then transferred to a vacuum evaporator.
  • a solvent such as isopropyl alcohol, acetone, methanol or the like
  • HAT hexaazatriphenylene
  • NPB N-(1-naphthyl)-N-phenylamino]biphenyl
  • lithium fluoride (LiF) and aluminum were sequentially deposited to thicknesses of 12 ⁇ and 2,000 ⁇ , respectively, to form a cathode.
  • the deposition rate of the organic materials was maintained at 0.4-0.7 ⁇ /sec
  • the deposition rates of lithium fluoride and aluminum for the cathode were maintained at 0.3 ⁇ /sec and 2 ⁇ /sec, respectively
  • the strength of the vacuum during the deposition was maintained at 2 ⁇ 10 ⁇ 7 to 5 ⁇ 10 ⁇ 6 torr.

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Abstract

The present disclosure provides a novel compound capable of greatly improving the lifetime, efficiency, electrochemical stability and thermal stability of an organic electronic device, and an organic electronic device including an organic compound layer containing the compound.

Description

This application is a Divisional of U.S. patent application Ser. No. 14/406,739, filed on Dec. 9, 2014 which is a National Phase Application of International Application No. PCT/KR2013/004231, filed on May 13, 2013, which claims the benefit of Korean Application No. 10-2012-0076493, filed on Jul. 13, 2012 and Korean Application No. 10-2013-0053966, filed on May 13, 2013, all of which are hereby incorporated by reference in their entirety for all purposes as if fully set forth herein.
TECHNICAL FIELD
The present disclosure relates to a novel heterocyclic compound and to an organic electronic device comprising the same.
BACKGROUND ART
As used herein, the term “organic electronic device” refers to a device that requires the exchange of an electronic charge between an electrode and an organic material using holes and/or electrons. The organic electronic device can be largely classified according to its operational principle into two types as follows. One type is an electronic device having a configuration in which an exciton is formed in an organic material layer by the entry of photons into the device from an external light source, and is then separated into an electron and a hole, which are transferred to different electrodes as a current source (voltage source), and the other type is an electric device having a configuration in which a voltage or a current is applied to two or more electrodes to inject a hole and/or an electron into an organic semiconductor positioned at the interface between the electrodes, and the device is operated using the injected electron and hole.
Examples of the organic electronic device include an organic light-emitting device, an organic solar cell, an organic transistor and the like, all of which require a hole-injecting or hole-transporting material, an electron-injecting or electron-transporting material or a light emitting material to drive the device. Hereinafter, the organic light-emitting device will be mainly and specifically described, but in the above-mentioned organic electronic devices, the hole-injecting or hole-transporting material, the electron-injecting or electron-transporting material, or the light-emitting material injection functions according to a similar principle.
In general, the term “organic light-emitting phenomenon” refers to a phenomenon in which electric energy is converted to light energy using an organic material. The organic light-emitting device that uses the organic light-emitting phenomenon usually has a structure comprising an anode, a cathode and an organic material layer interposed therebetween. Herein, the organic layer often has a multilayer structure consisting of a plurality of layers made of different materials in order to increase the efficiency and stability of the organic light-emitting device. For example, the organic material layer may consist of a hole-injecting layer, a hole-transporting layer, a light-emitting layer, an electron-transporting layer, an electron-injecting layer and the like. In the organic-light emitting device having this structure, when a voltage is applied between two electrodes, holes from the anode and electrons from the cathode are injected into the organic material layer, and the injected holes and electrons are combined with each other to form excitons. When the excitons subsequently drop to the ground state, light is emitted.
The development of novel materials for organic light-emitting devices as described above has been continuously demanded, and the development of materials for other organic electronic devices as described above has also been demanded.
PRIOR ART DOCUMENTS Patent Documents
International Patent Application Publication No. WO 2003/012890
DISCLOSURE Technical Problem
Accordingly, it is an object of the present disclosure to provide a heterocyclic compound having a chemical structure, which, depending on the substituent groups thereof, may provide various functions required for an organic electronic device, and to provide an organic electronic device comprising the same.
Technical Solution
The present disclosure provides the compound represented by the following formula 1:
Figure US09882146-20180130-C00001
wherein
  • n is 2,
  • X1 to X3 are the same or different, and are each independently a trivalent heteroatom or CH, and at least one of X1 to X3 is a trivalent heteroatom,
  • Ar1 and Ar2 are the same or different, and are each independently a substituted or unsubstituted aryl group or a heterocyclic group,
  • L is a direct bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted alkenylene group, a substituted or unsubstituted fluorenylene group or a substituted or unsubstituted heterocyclic group having a heteroatom selected from O, N, S and P, and
  • Ar3 is selected from the group consisting of a substituted or unsubstituted 2,7-naphthyl group, a substituted or unsubstituted 1,2-naphthyl group, a substituted or unsubstituted 1,3-naphthyl group, a substituted or unsubstituted 1,6-naphthyl group, a substituted or unsubstituted 1,7-naphthyl group, a substituted or unsubstituted 1,8-naphthyl group, a substituted or unsubstituted 2,3-naphthyl group, a substituted or unsubstituted 3,6-fluorenyl group and a substituted or unsubstituted 1,8-fluorenyl group.
The present disclosure also provides an organic electronic device comprising a first electrode, a second electrode and one or more organic material layers interposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprise the heterocyclic compound of formula 1.
Advantageous Effects
The novel compound according to the present invention may be used as a material for the organic material layer of organic electronic devices, including organic light-emitting devices. The use of the novel compound according to the present invention makes it possible to improve the efficiency of organic electronic devices including organic light-emitting devices, lower the driving voltage of the devices, and/or increase the lifetime of the devices.
DESCRIPTION OF DRAWINGS
FIG. 1 shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4.
FIG. 2 shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a hole-injecting layer 5, a hole-transporting layer 6, a light-emitting layer 7, an electron-transporting layer 8 and a cathode 4.
 MODE FOR INVENTION
The present disclosure provides the compound represented by formula 1.
In the present disclosure, examples of the trivalent heteroatom include, but are not limited to, N and P.
In an embodiment of the present disclosure, the trivalent heteroatom is N.
In an embodiment of the present disclosure, X1 to X3 are the same or different, and are each independently N or CH, and at least one of X1 to X3 is N.
In an embodiment of the present disclosure, n is 2.
In an embodiment of the present disclosure, when n is 2, X1 to X3, Ar1 to Ar3 and L may be the same or different.
In an embodiment of the present disclosure, Ar3 is selected from among the following structures:
Figure US09882146-20180130-C00002
wherein a, c, d and e are each an integer ranging from 1 to 6,
  • b and b′ are each an integer ranging from 1 to 3,
  • R1 to R6 are the same or different, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthioxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted arylsulfoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aralkylamine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heteroarylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazole group, or a substituted or unsubstituted heterocyclic group containing at least one heteroatom selected from among N, O, S and P,
  • R′ and R″ are the same or different, and are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthioxy group, substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted arylsulfoxy group, substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, substituted or unsubstituted boron group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aralkylamine group, substituted or unsubstituted arylamine group, a substituted or unsubstituted heteroarylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazole group, and a substituted or unsubstituted heterocyclic group containing at least on selected from among N, O, S and P atoms, or may form a condensed ring with an aliphatic, aromatic, aliphatic heterocyclic or aromatic heterocyclic ring, or may form a spiro linkage.
In the present disclosure, “
Figure US09882146-20180130-P00001
” means a portion linked to another substituent group. In an embodiment,
Figure US09882146-20180130-P00001
may be linked to L of formula 1. In another embodiment, it may be linked to a heterocyclic ring containing X1 to X3, when L is a direct bond.
In an embodiment of the present disclosure, Ar1 and Ar2 are the same or different, and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted pyridine group.
In another embodiment, L is a direct bond or a substituted or unsubstituted phenylene group.
Examples of the substituent groups will be described below, but are not limited thereto.
In the present disclosure, the alkyl group may be linear or branched, and the number of carbon atoms thereof is not specifically limited, but preferably ranges from 1-50. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl and heptyl groups.
In the present disclosure, the alkenyl group may be linear or branched, and the number of carbon atoms thereof is not specifically limited, but preferably ranges from 2-50. Specific examples of the alkenyl group include, but are not limited to, aryl-substituted alkenyl groups such as stylbenyl and styrenyl groups.
In the present disclosure, the alkoxy group may be linear or branched, and the number of carbon atoms thereof is not specifically limited, but preferably ranges from 1-50.
The lengths of the alkyl, alkenyl and alkoxy groups in the compound do not influence the conjugation length of the compound, but merely influence the method used to apply the compound to an organic electronic device, for example, a vacuum deposition method or a solution application method, and thus the numbers of carbon atoms of these groups are not specifically limited.
In the present disclosure, the cycloalkyl group is not specifically limited, but preferably contains 3-60 carbon atoms. Preferred examples of the cycloalkyl group include cyclopentyl and cyclohexyl groups.
In the present disclosure, examples of the halogen group include fluorine, chlorine, bromine or iodine.
In the present disclosure, the fluorenyl group has a structure in which two cyclic organic compounds are linked to each other by one atom, and examples thereof include
Figure US09882146-20180130-C00003
and the like.
In the present disclosure, the fluorenyl groups include an open fluorenyl group having a structure in which one of two cyclic compounds linked to each other by one atom is broken. Examples of the open fluorenyl group include
Figure US09882146-20180130-C00004
and the like.
In the present disclosure, the number of carbon atoms of the amine group is not specifically limited, but preferably ranges from 1-50. Specific examples of the amine group include, but are not limited to, methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl-anthracenylamine, diphenylamine, phenylnapthylamine, ditolylamine, phenyltolylamine and triphenylamine groups.
In the present disclosure, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group or a substituted or unsubstituted triarylamine group. The aryl group of the arylamine group may be a monocyclic or polycyclic aryl group. The arylamine group containing two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or both the monocyclic aryl group and the polycyclic aryl group.
Specific examples of the arylamine group include, but are not limited phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methyl-phenylamine, 4-methyl-naphthylamine, 2-methyl-biphenylamine, 9-methyl-anthracenylamine, diphenlamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, carbazole and triphenylamine groups.
In the present disclosure, the number of carbon atoms of each of the aryloxy, arylthioxy, arylsulfoxy and aralkylamine groups is not specifically limited, but preferably ranges from 6-50. The aryl group of each of the aryloxy, arylthioxy, arylsulfoxy and aralkylamine groups is as defined above.
In the present disclosure, the alkyl group of each of the alkylthioxy, alkylsulfoxy, alkylamine and aralkylamine groups is as defined above.
In the present disclosure, the heteroaryl group of the heteroarylamine group may be selected from the above-described examples of the heterocyclic group.
In the present disclosure, the arylene, alkenylene, fluorenylene and heteroarylene groups are divalent aryl, alkenyl, fluorenyl and heteroaryl groups, respectively. These groups are as defined above for the aryl, alkenyl, fluorenyl and heteroaryl groups, except that they are divalent groups.
As used herein, the term “substituted or unsubstituted” means that it is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, a silyl; group, an arylalkenyl group, an aryl group, an aryloxy group, an alkylthioxy group, an alkylsulfoxy group, an arylsulfoxy group, a boron group, an alkylamine group, an aralkylamine group, an arylamine group, a heteroaryl group, a carbazole group, an arylamine group, a fluorenyl group, a nitrile group, a nitro group, a hydroxyl group, a cyano group and a heterocyclic group containing at least one heteroatom selected from among N, O, S and P.
The present disclosure provides a novel heterocyclic compound represented by formula 1 above. This compound may be used for an organic material layer in an organic electronic device due to its structural specificity.
In an embodiment, Ar3 is a substituted or unsubstituted 2,7-naphthyl group, a substituted or unsubstituted 1,8-naphthyl group, a substituted or unsubstituted 1,6-naphthyl group, a substituted or unsubstituted 1,7-naphthyl group, or a substituted or unsubstituted 3,6-fluorenyl group.
In an embodiment of the present disclosure, Ar3 is a 2,7-naphthyl group.
In another embodiment, Ar3 is a 1,8-naphthyl group.
In still another embodiment, Ar3 is a 1,7-naphthyl group.
In still another embodiment, Ar3 is a 1,6-naphthyl group.
In an embodiment of the present disclosure, Ar3 is a 3,6-fluorenyl group. In this case, the effect of the compound as an electron donor can be further increased to increase the efficiency with which an electron is transported to and injected into a light-emitting layer. For this reason, the compound may have excellent characteristics in terms of voltage and efficiency.
In an embodiment of the present disclosure, Ar3 is a 2,7-naphthyl group substituted with an aryl group.
In an embodiment of the present disclosure, Ar3 is a 2,7-naphthyl group substituted with a phenyl group.
In an embodiment of the present disclosure, Ar3 is a 1,8-naphthyl group substituted with an aryl group.
In an embodiment of the present disclosure, Ar3 is a 1,8-naphthyl group substituted with a phenyl group.
In an embodiment of the present disclosure, Ar3 is a 1,7-naphthyl group substituted with an aryl group.
In an embodiment of the present disclosure, Ar3 is a 1,7-naphthyl group substituted with a phenyl group.
In an embodiment of the present disclosure, Ar3 is a 1,6-naphthyl group substituted with an aryl group.
In an embodiment of the present disclosure, Ar3 is a 1,6-naphthyl group substituted with a phenyl group.
In an embodiment of the present disclosure, the compound represented by formula 1 is represented by any one of the following formulas 1-a, 1-b, 1-c, 1-d and 1-e:
Figure US09882146-20180130-C00005
wherein
  • Ar1, Ar2, L and X1 to X3 are as defined in formula 1,
  • Ar1′, Ar2′, L′ and X1′ to X3′ are the same as the definitions of Ar1, Ar2, L and X1 to X3, respectively, and
  • R1 to R6, a, b, b′, c, d and e are as defined above.
In an embodiment of the present disclosure, at least one of X1 to X3 in formula 1 may be a trivalent heteroatom.
Specifically, at least one of X1 to X3 may be N or P.
In an embodiment of the present disclosure, X1 to X3 may all be N.
In an embodiment of the present disclosure, X1 may be N, and X2 and X3 may be CH.
In an embodiment of the present disclosure, X2 may be N, and X1 and X3 may be CH.
In an embodiment of the present disclosure, X3 may be N, and X1 and X2 may be CH.
In an embodiment of the present disclosure, X1 and X2 may be N. In this case, X3 is CH.
In an embodiment of the present disclosure, X1 and X3 may be N. In this case, X2 is CH.
In an embodiment of the present disclosure, X2 and X3 may be N. In this case, X1 is CH.
In an embodiment of the present disclosure, when n in formula 1 is 2, the structures linked to Ar3 may be the same or different.
In another embodiment of the present disclosure, Ar1 and Ar2 in formula 1 may be substituted or unsubstituted aryl or heteroaryl groups.
Specifically, Ar1 and Ar2 may be the same or different, and may be each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridyl group or a substituted or unsubstituted naphthyl group.
In an embodiment of the present disclosure, Ar1 and Ar2 are the same or different, and may be each independently an alkyl-substituted phenyl group, an alkoxy-substituted phenyl group, a halogen-substituted phenyl group or a trifluoro-substituted phenyl group.
In an embodiment of the present disclosure, Ar1 and Ar2 are the same or different, and may be each independently an alkyl-substituted biphenyl group, an alkoxy-substituted biphenyl group, a halogen-substituted biphenyl group or a trifluoro-substituted biphenyl group.
In an embodiment of the present disclosure, Ar1 and Ar2 are the same or different, and may be each independently an alkyl-substituted pyridyl group, an alkoxy-substituted pyridyl group, a halogen-substituted pyridyl group or a trifluoro-substituted pyridyl group.
In an embodiment of the present disclosure, Ar1 and Ar2 are the same or different, and may be each independently an alkyl-substituted phenyl group, an alkoxy-substituted naphthyl group, a halogen-substituted naphthyl group or a trifluoro-substituted naphthyl group.
In an embodiment of the present disclosure, Ar1 and Ar2 are the same or different, and may be each independently a methyl-substituted phenyl group, a methoxy-substituted phenyl group, a fluoro-substituted phenyl group or a trifluoro-substituted phenyl group.
In an embodiment of the present disclosure, Ar1 and Ar2 are the same or different, and may be each independently
Figure US09882146-20180130-C00006
wherein R0 may be selected from the group consisting of alkyl, alkoxy, halogen and trifluoro groups.
In an embodiment of the present disclosure, Ar1 and Ar2 are the same or different, and may be each independently a methyl-substituted biphenyl group, a methoxy-substituted biphenyl group, a fluoro-substituted biphenyl group or a trifluoro-substituted biphenyl group.
In an embodiment of the present disclosure, Ar1 and Ar2 are the same or different, and may be each independently a methyl-substituted pyridyl group, a methoxy-substituted pyridyl group, a fluoro-substituted pyridyl group or a trifluoro-substituted pyridyl group.
In an embodiment of the present disclosure, Ar1 and Ar2 are the same or different, and may be each independently a methyl-substituted naphthyl group, a methoxy-substituted naphthyl group, a fluoro-substituted naphthyl group or a trifluoro-substituted naphthyl group.
In an embodiment of the present disclosure, Ar1 and Ar2 are the same or different and may be each independently a phenyl, biphenyl, pyridyl or naphthyl group.
In an embodiment of the present disclosure, Ar1 and Ar2 are the same or different, and may be each independently
Figure US09882146-20180130-C00007
In an embodiment of the present disclosure, Ar1 and Ar2 are the same or different, and may be each independently
Figure US09882146-20180130-C00008
In an embodiment of the present disclosure, Ar1 and Ar2 are the same or different, and may be each independently
Figure US09882146-20180130-C00009
In an embodiment of the present disclosure, Ar1 and Ar2 are the same or different, and may be each independently
Figure US09882146-20180130-C00010
In an embodiment of the present disclosure, Ar1 and Ar2 are the same or different, and may be each independently
Figure US09882146-20180130-C00011
In an embodiment of the present disclosure, Ar1 and Ar2 are the same or different, and may be each independently
Figure US09882146-20180130-C00012
In the present disclosure, “
Figure US09882146-20180130-P00001
” means that Ar1 or Ar2 is linked to the heterocyclic ring including X1 to X3 of formula 1.
In another embodiment of the present disclosure, L may be a direct bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted alkenylene group, a substituted or unsubstituted fluorenylene group or a substituted or unsubstituted heteroarylene having a heteroatom selected from among O, N, S and P.
Specifically, L may be a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted pyridylene group or a substituted or unsubstituted biphenylene group.
In an embodiment of the present disclosure, L may be a phenylene, naphthalene, fluorenylene, pyridylene or biphenylene group.
In an embodiment of the present disclosure, L may be a direct bond.
In an embodiment of the present disclosure, L may be a phenylene group. Specifically, L may be
Figure US09882146-20180130-C00013
In another embodiment, L may be
Figure US09882146-20180130-C00014
Herein, “
Figure US09882146-20180130-P00001
” means that L is linked to either the heterocyclic ring including X1 to X3 of formula 1 or Ar3.
In an embodiment of the present disclosure, the compound represented by formula 1 is any one of the following compounds 1-a-1 to 1-a-16, 2-a-1 to 2-a-11, 3-a-1 to 3-a-4, 1-b-1 to 1-b-16, 2-b-1 to 2-b-11, 3-b-1 to 3-b-4, 1-c-1 to 1-c-16, 2-c-1 to 2-c-11, 3-c-1 to 3-c-4, 1-d-1 to 1-d-16, 2-d-1 to 2-d-11, 3-d-1 to 3-d-4, 1-e-1 to 1-e-10, and 2-e-1 to 2-e-8.
In an embodiment of the present disclosure, the compound represented by formula 1-a is any one of the following compounds 1-a-1 to 1-a-16, 2-a-1 to 2-a-11 and 3-a-1 to 3-a-4:
Figure US09882146-20180130-C00015
Figure US09882146-20180130-C00016
Figure US09882146-20180130-C00017
Figure US09882146-20180130-C00018
Figure US09882146-20180130-C00019
Figure US09882146-20180130-C00020
Figure US09882146-20180130-C00021
In an embodiment of the present disclosure, the compound represented by formula 1-b is any one of the following compounds 1-b-1 to 1-b-16, 2-b-1 to 2-b-11 and 3-b-1 to 3-b-4.
Figure US09882146-20180130-C00022
Figure US09882146-20180130-C00023
Figure US09882146-20180130-C00024
Figure US09882146-20180130-C00025
Figure US09882146-20180130-C00026
Figure US09882146-20180130-C00027
In an embodiment of the present disclosure, the compound represented by formula 1-c is any one of the following compounds 1-c-1 to 1-c-16, 2-c-1 to 2-c-11 and 3-c-1 to 3-c-4.
Figure US09882146-20180130-C00028
Figure US09882146-20180130-C00029
Figure US09882146-20180130-C00030
Figure US09882146-20180130-C00031
Figure US09882146-20180130-C00032
Figure US09882146-20180130-C00033
Figure US09882146-20180130-C00034
In an embodiment of the present disclosure, the compound represented by formula 1-d is any one of the following compounds 1-d-1 to 1-d-16, 2-d-1 to 2-d-11 and 3-d-1 to 3-d-4:
Figure US09882146-20180130-C00035
Figure US09882146-20180130-C00036
Figure US09882146-20180130-C00037
Figure US09882146-20180130-C00038
Figure US09882146-20180130-C00039
Figure US09882146-20180130-C00040
Figure US09882146-20180130-C00041
Figure US09882146-20180130-C00042
Figure US09882146-20180130-C00043
Figure US09882146-20180130-C00044
In an embodiment of the present disclosure, the compound represented by formula 1-e is any one of the following compounds 1-e-1 to 1-e-10 and 2-e-1 to 2-e-8:
Figure US09882146-20180130-C00045
Figure US09882146-20180130-C00046
Figure US09882146-20180130-C00047
Figure US09882146-20180130-C00048
Figure US09882146-20180130-C00049
Figure US09882146-20180130-C00050
Figure US09882146-20180130-C00051
The compound of formula 1 may have suitable characteristics for use as an organic material layer in an organic electronic device as a result of introducing various substituents into the heterocyclic structure, which is the core structure shown in formula 1.
The conjugation length and energy band gap of a compound have a close relationship with each other. Specifically, as the conjugation length of a compound increases, the energy band gap decreases. As described above, the core structure of the compound of formula 1 has a limited conjugation length, and thus has a high energy band gap.
In the present disclosure, compounds having various energy band gaps can be synthesized by introducing various substituents into the positions Ar1 to Ar3 and R1 to R6 of the core structure having a high energy band gap as described above. It is generally easy to control the energy band gap by introducing the substituents of a core structure having a high energy band gap. However, when a core structure has a low energy band gap, it is difficult to control the energy band gap so as to have a high level by introducing substituents into the core structure. In addition, in the present disclosure, the HOMO and LUMO energy levels of the compound can also be controlled by introducing various substituents into the positions of Ar1 to Ar3 and R1 to R6 of the above-described core structure.
Moreover, when various substituents are introduced into the above-described core structure, a compound having the inherent characteristics of the introduced substituents can be synthesized. For example, when substituents which are mainly used in materials for the hole-injecting layer, hole-transporting layer, light-emitting layer and electron-transporting layer of an organic electronic device are introduced into the above-described core structure, a material that satisfies the conditions required for each of the organic material layers can be synthesized.
Because the compound of formula 1 includes the heterocyclic structure in the core structure, it may have a suitable energy level for use as a hole-injecting material and/or a hole-transporting material in an organic light-emitting device. In the present disclosure, when a compound having a suitable energy level, attributable to the substituents introduced therein, is selected from among the compounds of formula 1 and used in an organic light-emitting device, the device may have a low driving voltage and a high optical efficiency.
In addition, when various substituents, particularly hydrogen or deuterium, are introduced into the core structure, the energy band gap can be finely controlled, while the characteristics of the interface between organic materials in an organic electron device can be improved and the compound of formula 1 may be used in various applications.
Meanwhile, the compound of formula 1 has excellent thermal stability due to its high glass transition temperature (Tg). This increase in the thermal stability is an important factor that provides driving stability to a device.
The compound of formula 1 can be prepared based on Preparation Examples, which will be described below.
The heterocyclic compound of formula 1 can be prepared by substituting the heterocyclic ring of formula 1, which includes X1 to X3, with Ar1, Ar2 and L, and then bonding the two substituted heterocyclic rings, which include X1 to X3, to Ar3.
In addition to the compounds represented by formulas 1-a-1 to 1-a-16, 2-a-1 to 2-a-11, 3-a-1 to 3-a-4, 1-b-1 to 1-b-16, 2-b-1 to 2-b-11, 3-b-1 to 3-b-4, 1-c-1 to 1-c-16, 2-c-1 to 2-c-11, 3-c-1 to 3-c-4, 1-d-1 to 1-d-16, 2-d-1 to 2-d-11, 3-d-1 to 3-d-4, 1-e-1 to 1-e-10 and 2-e-1 to 2-e-8, other compounds represented by formula 1 can be prepared by changing the number of heteroatoms of X1 to X3 and the substituent groups of Ar1 to Ar3 and L.
The present disclosure also provides an organic electronic device comprising the compound of formula 1.
In an embodiment of the present disclosure, the organic electronic device may have a structure comprising a first electrode, a second electrode and one or more organic material layers interposed between the first and second electrodes.
The organic electronic device may be selected from the group consisting of an organic light-emitting device, an organic solar cell and an organic transistor.
In an embodiment of the present disclosure, the organic electronic device may be an organic light-emitting device.
In an embodiment of the present disclosure, there is provided an organic light-emitting device comprising a first electrode, a second electrode and one or more organic material layers interposed between the first and second electrodes, wherein one or more of the organic layers comprise the heterocyclic compound represented by formula 1.
The organic material layers of the organic light-emitting device according to the present disclosure may have a single-layer structure or a multilayer structure consisting of two or more organic layers. For example, the organic light-emitting device according to the present disclosure may have a structure comprising organic material layers, including a hole-injecting layer, a hole-transporting layer, a light-emitting layer, an electron-transporting layer and an electron-injecting layer. However, the structure of the organic light-emitting device is not limited thereto, and may comprise a smaller number of organic material layers.
Thus, in another embodiment of the present disclosure, the organic material layers of the organic light-emitting device may include one or more of a hole-injecting layer, a hole-transporting layer and a layer that performs both hole injection and hole transport, and one or more of the layers may comprise the compound represented by formula 1.
Specifically, the organic material layers of the organic light-emitting device may include a hole-injecting layer, which may comprise the compound represented by formula 1. In another embodiment, the organic material layers of the organic light-emitting device may include a hole-transporting layer, which may comprise the compound represented by formula 1. In still another embodiment, the organic material layers of the organic light-emitting device may include a hole-transporting layer and a hole-injecting layer, in which the hole-transporting layer and the hole-injecting layer may comprise the compound represented by formula 1.
In addition, the organic material layers may include a light-emitting layer, in which the light-emitting layer may comprise the compound represented by formula 1. In an embodiment, the compound represented by formula 1 may be included as a host in the light-emitting layer. In another embodiment, the organic material layer comprising the compound represented by formula 1 may include the compound of formula 1 as a host, and may include another organic compound, a metal or a metal compound as a dopant.
In addition, the organic material layers may include one or more of an electron-transporting layer, an electron-injecting layer or a layer that performs both electron transport and electron injection, wherein one or more of the layers may comprise the compound represented by formula 1.
Specifically, the organic material layers of the organic light-emitting device may include an electron-injecting layer, wherein the electron-injecting layer may comprise the compound represented by formula 1. In another embodiment, the organic material layers of the organic light-emitting device may include an electron-transporting layer, wherein the electron-transporting layer may comprise the compound represented by formula 1. In still another embodiment, the organic material layers of the organic light-emitting device may include an electron-transporting layer and an electron-injecting layer, wherein the electron-transporting layer and the electron-injecting layer may comprise the compound represented by formula 1.
In this multilayer organic layer structure, the compound represented by formula 1 may be included in the light-emitting layer, the layer that performs all hole injection, hole transport and light emission, the layer that performs both hole transport and light emission, or the layer that performs both electron transport and light emission.
In another embodiment, the organic material layers of the organic light-emitting device may include, in addition to the organic material layer comprising the heterocyclic composition represented by formula 1, a hole-injecting layer or a hole-transporting layer, which comprises a compound containing an arylamino group, a carbazole group or a benzcarbazole group.
In an embodiment of the present disclosure, the organic electronic device may be an organic solar cell.
In an embodiment of the present disclosure, there is provided an organic solar cell comprising a first electrode, a second electrode and one or more organic material layers, including a photoactive layer, interposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprise the heterocyclic compound represented by formula 1.
In an embodiment of the present disclosure, the organic solar cell may include an electron-transporting layer, wherein the electron-transporting layer may comprise the compound represented by formula 1.
In another embodiment, the photoactive layer may comprise the compound represented by formula 1.
In still another embodiment, the organic solar cell may include a photoactive layer, an electron donor and an electron acceptor, wherein the photoactive layer, the electron donor and the electron acceptor may comprise the compound represented by formula 1.
In an embodiment of the present disclosure, when the organic solar cell receives a photon from an external light source, an electron and a hole are generated between the electron donor and the electron acceptor. The generated hole is transported to the anode through the electron donor layer.
In an embodiment of the present disclosure, the organic solar cell may further include an additional organic material layer. The organic solar cell may comprise a material having various functions in order to reduce the number of organic material layers therein.
In an embodiment of the present disclosure, the organic electronic device may be an organic transistor.
In an embodiment of the present disclosure, there is provided an organic transistor comprising a source, a drain, a gate and one or more organic material layers.
In an embodiment of the present disclosure, the organic transistor may include a charge-generating layer, wherein the charge-generating layer may comprise the compound represented by formula 1.
In another embodiment of the present disclosure, the organic transistor may include an insulating layer, wherein the insulating layer may be located on a substrate and the gate.
When the organic electronic device includes a plurality of organic material layers, the organic material layers may be formed of the same or different materials.
In an embodiment of the present disclosure, the organic electronic device may have the structures shown in FIGS. 1 and 2, but is not limited thereto.
FIG. 1 illustrates an organic electronic device having a structure in which a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4 are sequentially deposited. In this structure, the compound of formula 1 may be included in the light-emitting layer 3.
FIG. 2 illustrates an organic electronic device having a structure in which a substrate 1, an anode 2, a hole-injecting layer 5, a hole-transporting layer 6, a light-emitting layer 7, an electron-transporting layer 8 and a cathode 4 are sequentially deposited. In this structure, the compound represented by formula 1 may be included in one or more of the hole-injecting layer 5, the hole-transporting layer 6, the light-emitting layer 7 and the electron-transporting layer 8.
The organic electronic device according to the present disclosure can be fabricated using the same materials and method as known in the art, except that one or more of the organic material layers may comprise the compound of the present disclosure, that is, the compound of formula 1.
For example, the organic electronic device according to the present disclosure can be fabricated by sequentially depositing a first electrode, one or more organic material layers and a second electrode on a substrate. Specifically, the organic electronic device can be fabricated by depositing a metal, a conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form an anode, forming organic material layers, including a hole-injecting layer, a hole-transporting layer, a light-emitting layer and an electron-transporting layer, on the anode, and then depositing thereon a material that may be used to form a cathode. In addition, the organic electronic device may also be fabricated by sequentially depositing a cathode material, one or more organic material layers and an anode material on the substrate.
In addition, during the fabrication of the organic electronic device, the compound of formula 1 can be formed into an organic material layer using a solution application method in addition to the physical vacuum deposition method. As used herein, the term “solution application method” refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating or the like, but is not limited thereto.
In addition, the organic electronic device can also be fabricated by sequentially depositing a cathode material, organic material layers and an anode material on a substrate (International Patent Application Publication No. WO 2003/012890). However, the fabrication method is not limited to the above methods.
The anode material is preferably a material having a high work function, so that holes can be easily injected into the organic material layers. Specific examples of an anode material that may be used in the present invention include, but are not limited to, metals such as vanadium, chromium, copper, zinc or gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) or indium zinc oxide (IZO); metal/oxide combinations such as ZnO: Al or SNO2: Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline.
The cathode material is preferably a material having a low work function, so that electrons are easily injected into the organic material layers. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and multilayer materials such as LiF/Al or LiO2/Al.
The hole-injecting material is a material that can easily receive holes from the anode at a low voltage, and the HOMO (highest occupied molecular orbital) of the hole-injecting material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layers. Specific examples of the hole-injecting material include, but are not limited to, metal porphyrin, oligothdophene, and arylamine-based organic materials, hexanitrile hexaazatriphenyiene and quinacridone-based organic materials, perylene-based organic materials, anthraquinone, polyandline-based or polythiophene-based conductive polymers and the like.
The hole-transporting material is preferably a material having high hole mobility, which is capable of transferring holes from the anode or the hole-injecting layer to the light-emitting layer. Specific examples of the hole-transporting material include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated portions and non-conjugated portions.
The light-emitting material a material capable of emitting visible light, by receiving holes and electrons from the hole-transporting layer and from the electron-transporting layer and combining the received holes and electrons, and is preferably a material having high quantum efficiency for fluorescence and phosphorescence. Specific examples of the light emitting material include, but are not limited to, an 8-hydroxyquinoline aluminum complex (Alg3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole-, benzthiazole- and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; and compounds such as polyfluorene and rubrene.
The electron-transporting material is a material that can easily receive electrons from the cathode and transfer the received electrons to the light-emitting layer. It is preferably a material having high electron mobility. Specific examples of the electron-transporting material include, but are not limited to, a 8-hydroxyquinoline aluminum complex; complexes including Alg3; organic radical compounds; and hydroxyflavone-metal complexes.
The organic electronic device according to the present disclosure may be a front side light-emitting type, a rear side light-emitting type or a both-side light-emitting type, depending on the material used.
EXAMPLES
Hereinafter, the present disclosure will be described in further detail with reference to Preparation Examples and Experimental Examples, but the scope of the present disclosure is not limited by these Preparation Examples and Experimental Examples.
PREPARATION EXAMPLES Preparation Example 1: Preparation of Compound 1-a-1
1) Synthesis of Compound 1-A
Figure US09882146-20180130-C00052
Magnesium (9.7 g, 0.40 mol) and iodine (1.02 g, 8 mmol) were suspended in 80 ml of an anhydrous tetrahydrofuran solvent in a nitrogen atmosphere to prepare a suspension, and a solution of bromobenzene (62.8 g, 0.4 mol) in 150 ml of anhydrous tetrahydrofuran was slowly added dropwise to the suspension over 1 hour. The mixture was heated under reflux for 3 hours. The mixture was cooled to room temperature, and then a solution of 1,3,5-trichlorotriazine (27.6 g, 0.15 mol) in 150 ml of anhydrous tetrahydrofuran was slowly added dropwise to the mixture, which was then stirred under reflux for about 5 hours. After completion of the reaction, the organic solvent in the reaction solution was removed by distillation under reduced pressure, and the residue was recrystallized from ethanol, thereby obtaining compound 1-A (39 g, yield: 73.5%).
MS[M+H]+=268
2) Synthesis of Compound 1-B
Figure US09882146-20180130-C00053
Compound 1-A (37.1 g, 0.14 mol) and 4-chlorophenylboronic acid (23.8 g, 0.15 mol) were completely dissolved in 150 ml of tetrahydrofuran in a nitrogen atmosphere, and then 80 ml of a 2M aqueous solution of potassium carbonate was added thereto, and tetrakis-(triphenylphosphine)palladium (3.2 g, 2.7 mmol) was added thereto. Then, the mixture was heated with stirring for 5 hours. The temperature of the mixture was lowered to room temperature, and the aqueous layer was removed. The residue was dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by column chromatography using tetrahydrofuran:hexane=1:6, thereby obtaining compound 1-B (34 g, yield: 72%).
MS[M+H]+=344
3) Synthesis of Compound 1-C
Figure US09882146-20180130-C00054
Compound 1-B (34 g, 98.9 mmol), bis(pinacolate)diboron (27.6 g, 108 mmol) and potassium acetate (29.1 g, 296 mmol) were mixed with each other in a nitrogen atmosphere, and the mixture was added to 100 ml of dioxane and heated with stirring. Bis(dibenzylideneacetone)palladium (1.7 g, 2.94 mmol) and tricyclohexylphosphine (1.6 g, 5.9 mmol) were added to the mixture under reflux and heated with stirring for 10 hours. After completion of the reaction, the reaction solution was cooled to room temperature and filtered. The filtrate was added to water and extracted with chloroform, and the organic layer was dried with anhydrous magnesium sulfate. The resulting material was distilled under reduced pressure and recrystallized from ethanol, thereby obtaining compound 1-C (35 g, yield: 81%).
MS[M+H]+=436
4) Synthesis of Compound 1-a-1
Figure US09882146-20180130-C00055
Compound 1-C (16.4 g, 37.7 mmol) and 2,7-dibromonaphthalene (5.1 g, 17.9 mmol) were completely dissolved in tetrahydrofuran (50 ml), and a 2M potassium carbonate aqueous solution (30 ml) and tetrakistriphenyl-phosphine palladium (400 mg, 0.34 mmol) were added thereto. The mixture was heated with stirring for 2 hours. Then, the mixture was cooled to room temperature to complete the reaction, after which the potassium carbonate solution was removed and the white solid was filtered. The white solid was washed once with each of tetrahydrofuran and ethanol, thereby obtaining compound 1-a-1 (12.0 g, yield 92%).
MS[M+H]+=743
Preparation Example 2: Preparation of Compound 1-a-7
1) Synthesis of Compound 2-A
Figure US09882146-20180130-C00056
Compound 1-A (30.0 g, 0.11 mol) and 3-chlorophenylboronic acid (19.2 g, 0.12 mol) were completely dissolved in 200 ml of tetrahydrofuran in a nitrogen atmosphere, and then a 2M potassium carbonate aqueous solution (100 ml) and tetrakis-(triphenylphosphine)palladium (2.5 g, 2.2 mmol) were added thereto. The mixture was heated with stirring for 6 hours. Then, the temperature of the mixture was lowered to room temperature, and the aqueous layer was removed. The residue was dried with anhydrous magnesium sulfate, concentrated under reduced pressure and purified by column chromatography using tetrahydrofuran:hexane=1:6, thereby obtaining compound 2-A (31 g, yield: 82%).
MS[M+H]+=344
2) Synthesis of Compound 2-B
Figure US09882146-20180130-C00057
Compound 2-A (14.5 g, 42.2 mmol), bis(pinacolate)diboron (12.9 g, 50.6 mmol) and potassium acetate (12.3 g, 1236 mmol) were mixed with each other in a nitrogen atmosphere, and the mixture was added to 100 ml of dioxane and heated with stirring. Bis(dibenzylideneacetone)palladium (727 mg, 1.26 mmol) and tricyclohexylphosphine (709 mg, 2.52 mmol) were added to the mixture under reflux and heated with stirring for 10 hours. After completion of the reaction, the reaction solution was cooled to room temperature and then filtered. The filtrate was added to water and extracted with chloroform, and the organic layer was dried with anhydrous magnesium sulfate. The resulting material was distilled under reduced pressure and then recrystallized from ethanol, thereby obtaining compound 2-B (17 g, 94%).
MS[M+H]+=436
3) Synthesis of Compound 1-a-7
Figure US09882146-20180130-C00058
Compound 2-B (17.3 g, 39.7 mmol) and 2,7-dibromonaphthalene (5.4 g, 18.9 mmol) were completely dissolved in 50 ml of tetrahydrofuran, and then a 2M potassium carbonate aqueous solution (30 ml) and tetrakistriphenyl-phosphine palladium (436 mg, 0.37 mmol) were added thereto. The mixture was heated with stirring for 2 hours. The temperature of the reaction mixture was cooled to complete the reaction, and then the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed once with each of tetrahydrofuran and ethanol, thereby obtaining compound 1-a-7 (12.2 g, yield: 87%).
MS[M+H]+=743
Preparation Example 3: Preparation of Compound 2-a-1
1) Synthesis of Compound 3-A
Figure US09882146-20180130-C00059
Compound 3-A was prepared in the same manner as compound 1-B, except that 4-chloro-2,6-diphenylpyrimidine was used instead of compound 1-A.
MS[M+H]+=343
2) Synthesis of Compound 3-B
Figure US09882146-20180130-C00060
Compound 3-B was prepared in the same manner as compound 1-C, except that compound 3-A was used instead of compound 1-B.
MS[M+H]+=435
3) Synthesis of Compound 2-a-1
Figure US09882146-20180130-C00061
Compound 2-a-1 was prepared in the same manner as compound 1-a-1, except that compound 3-B was used instead of compound 1-C.
MS[M+H]+=741
Preparation Example 4: Preparation of Compound 2-a-8
1) Synthesis of Compound 4-A
Figure US09882146-20180130-C00062
Compound 4-A was prepared in the same manner as compound 1-B, except that 3-chloro-2,6-diphenylpyrimidine was used instead of compound 1-A.
MS[M+H]+=341
2) Synthesis of Compound 4-B
Figure US09882146-20180130-C00063
Compound 4-B was prepared in the same manner as compound 1-C, except that compound 4-A was used instead of compound 1-B.
MS[M+H]+=435
3) Synthesis of Compound 2-a-8
Figure US09882146-20180130-C00064
Compound 2-a-8 was prepared in the same manner as compound 1-a-1, except that compound 4-B was used instead of compound 1-C.
MS[M+H]+=741
Preparation Example 5: Preparation of Compound 1-b-1
1) Synthesis of Compound 1-b-1
Figure US09882146-20180130-C00065
Compound 1-b-1 was prepared in the same manner as compound 1-a-1, except that 1,8-dibromonaphthalene was used instead of 2,7-dibromonaphthalene.
MS[M+H]+=743
Preparation Example 6: Preparation of Compound 1-c-1
1) Synthesis of Compound 1-c-1
Figure US09882146-20180130-C00066
Compound 1-c-1 was prepared in the same manner as compound 1-a-1, except that 1,6-dibromonaphthalene was used instead of 2,7-dibromonaphthalene.
MS[M+H]+=743
Preparation Example 7: Preparation of Compound 1-d-1
1) Synthesis of Compound 1-d-1
Figure US09882146-20180130-C00067
Compound 1-d-1 was prepared in the same manner as compound 1-a-1, except that 1,7-dibromonaphthalene was used instead of 2,7-dibromonaphthalene.
MS[M+H]+=743
Preparation Example 8: Preparation of Compound 1-e-1
1) Synthesis of Compound 1-e-1
Figure US09882146-20180130-C00068
Compound 1-e-1 was prepared in the same manner as compound 1-a-1, except that 3,6-dibromo-9,9-dimethyl-9H-fluorene was used instead of 2,7-dibromonaphthalene.
MS[M+H]+=809
Experimental Example 1
A glass substrate having ITO (indium tin oxide) coated thereon to a thickness of 1,000 Å was placed in distilled water containing a detergent dissolved therein, and was ultrasonically washed. Herein, the detergent was a product manufactured by Fischer Co., and the distilled water was distilled water filtered twice through a filter (Millipore Co.). After the ITO has been washed for 30 minutes, it was ultrasonically washed twice with distilled water for 10 minutes. After the completion of washing with distilled water, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, methanol or the like, and was dried, after which it was transported to a plasma cleaner. Then, the substrate was cleaned with oxygen plasma for 5 minutes, and then transferred to a vacuum evaporator.
On the transparent ITO electrode fabricated as described above, hexaazatriphenylene (HAT) having the following formula was deposited to a thickness of 500 Å by a thermal vacuum deposition method to form a hole-injecting layer:
Figure US09882146-20180130-C00069
On the hole-injecting layer, 4-4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) having the following formula, which is a hole-transporting material, was vacuum-deposited to a thickness of 400 Å to form a hole-transporting layer:
Figure US09882146-20180130-C00070
On the hole-transporting layer, a 25:1 (w/w) mixture of BH and BD, which have the following formulas, was vacuum-deposited to a thickness of 300 Å to form a light-emitting layer:
Figure US09882146-20180130-C00071
On the light-emitting layer, a 1:1 (w/w) mixture of compound 1-a-1, prepared in Preparation Example 1 as shown above, and lithium quinolate (LiQ), was vacuum-deposited to a thickness of 300 Å to form an electron-injecting and electron-transporting layer. On the electron-injecting and electron-transporting layer, lithium fluoride (LiF) and aluminum were sequentially deposited to thicknesses of 12 Å and 2,000 Å, respectively, to form a cathode.
In the above process for fabricating the organic light-emitting device, the deposition rate of the organic materials was maintained at 0.4-0.7 Å/sec, the deposition rates of lithium fluoride and aluminum for the cathode were maintained at 0.3 Å/sec and 2 Å/sec, respectively, and the strength of the vacuum during the deposition was maintained at 2×10−7 to 5×10−6 torr.
Experimental Example 2
An organic light-emitting device was fabricated in the same manner as described in Experimental Example 1, except that compound 1-a-7 was used instead of compound 1-a-1.
Experimental Example 3
An organic light-emitting device was fabricated in the same manner as described in Experimental Example 1, except that compound 2-a-1 was used instead of compound 1-a-1.
Experimental Example 4
An organic light-emitting device was fabricated in the same manner as described in Experimental Example 1, except that compound 2-a-8 was used instead of compound 1-a-1.
Experimental Example 5
An organic light-emitting device was fabricated in the same manner as described in Experimental Example 1, except that compound 1-b-1 was used instead of compound 1-a-1.
Experimental Example 6
An organic light-emitting device was fabricated in the same manner as described in Experimental Example 1, except that compound 1-c-1 was used instead of compound 1-a-1.
Experimental Example 7
An organic light-emitting device was fabricated in the same manner as described in Experimental Example 1, except that compound 1-d-1 was used instead of compound 1-a-1.
Experimental Example 8
An organic light-emitting device was fabricated in the same manner as described in Experimental Example 1, except that compound 1-e-1 was used instead of compound 1-a-1.
Comparative Example 1
An organic light-emitting device was fabricated in the same manner as described in Experimental Example 1, except that the following compound ET1 was used instead of compound 1-a-1:
Figure US09882146-20180130-C00072
Comparative Example 2
An organic light-emitting device was fabricated in the same manner as described in Experimental Example 1, except that the following compound ET2 was used instead of compound 1-a-1:
Figure US09882146-20180130-C00073
Comparative Example 3
An organic light-emitting device was fabricated in the same manner as described in Experimental Example 1, except that the following compound ET3 was used instead of compound 1-a-1:
Figure US09882146-20180130-C00074
Comparative Example 4
An organic light-emitting device was fabricated in the same manner as described in Experimental Example 1, except that the following compound ET4 was used instead of compound 1-a-1:
Figure US09882146-20180130-C00075
When an electric current was applied to each of the organic light-emitting devices fabricated in Experimental Examples 1 to 8 and Comparative Examples 1 to 4, the results shown in Table 1 below were obtained.
TABLE 1
Voltage Efficiency Color
(V@10 (cd/A@10 coordinates
Compound mA/cm2) mA/cm2) (x, y)
Experimental Compound 3.98 4.23 (0.138,
Example 1 1-a-1 0.127)
Experimental Compound 3.75 5.15 (0.139,
Example 2 1-a-7 0.122)
Experimental Compound 3.86 5.04 (0.138,
Example 3 2-a-1 0.126)
Experimental Compound 3.85 5.51 (0.138,
Example 4 2-a-8 0.127)
Experimental Compound 3.77 5.22 (0.137,
Example 5 1-b-1 0.125)
Experimental Compound 3.83 5.19 (0.136,
Example 6 1-c-1 0.127)
Experimental Compound 3.82 5.18 (0.136,
Example 7 1-d-1 0.127)
Experimental Compound 3.84 5.27 (0.136,
Example 8 1-e-1 0.125)
Comparative ET1 4.02 3.95 (0.136,
Example 1 0.130)
Comparative ET2 4.13 3.87 (0.136,
Example 2 0.126)
Comparative ET3 4.05 4.01 (0.135,
Example 3 0.125)
Comparative ET4 4.07 3.89 (0.135,
Example 4 0.130)
As can be seen in Table 1 above, the comparison between Experimental Examples 1 to 4 and Comparative Example 2 indicated that the ability to transport and inject electrons was excellent when Ar3 was 2,7-naphthyl compared to when Ar3 was 2,6-naphthyl.
As can be seen in Table 1 above, the comparison between Experimental Example 5 and Comparative Example 2 indicated that the ability to transport and inject electrons was excellent when Ar3 was 1,8-naphthyl compared to when Ar3 was 2,6-naphthyl.
As can be seen in Table 1 above, the comparison between Experimental Example 6 and Comparative Example 2 indicated that the ability to transport and inject electrons was excellent when Ar3 was 1,8-naphthyl compared to when Ar3 was 2,6-naphthyl.
As can be seen in Table 1 above, the comparison between Experimental Example 7 and Comparative Example 2 indicated that the ability to transport and inject electrons was excellent when Ar3 was 1,6-naphthyl compared to when Ar3 was 2,6-naphthyl.
As can be seen in Table 1 above, the comparison between Experimental Example 8 and Comparative Example 2 indicated that the ability to transport and inject electrons was excellent when Ar3 was 1,7-naphthyl compared to when Ar3 was 2,6-naphthyl.
As can be seen in Table 1 above, the comparison between Experimental Example 5 and Comparative Example 3 indicated that the ability to transport and inject electrons was excellent when Ar3 was 3,6-fluorenyl compared to when Ar3 was 2,7-fluorenyl.
The results in Table 1 above indicate that the compound according to the present disclosure has an excellent ability to transport and inject electrons, suggesting that it can be applied to an organic light-emitting device.

Claims (23)

The invention claimed is:
1. A heterocyclic compound represented by the following formula 1:
Figure US09882146-20180130-C00076
wherein
n is 2,
X1 to X3 are the same or different, and are each independently a N or CH, and two of X1 to X3 is a N,
Ar1 and Ar2 are the same or different, and are each independently a substituted or unsubstituted aryl group or a heterocyclic group,
L is a direct bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted alkenylene group, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted heterocyclic group having a heteroatom selected from O, N, S and P, and
Ar3 is selected from the group consisting of a substituted or unsubstituted 2,7-naphthyl group, a substituted or unsubstituted 1,2-naphthyl group, a substituted or unsubstituted 1,3-naphthyl group, a substituted or unsubstituted 1,6-naphthyl group, a substituted or unsubstituted 1,7-naphthyl group, a substituted or unsubstituted 1,8-naphthyl group, a substituted or unsubstituted 2,3-naphthyl group, a substituted or unsubstituted 3,6-fluorenyl group and a substituted or unsubstituted 1,8-fluorenyl group,
wherein the term of substituted or unsubstituted means that it is unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group, an aryl group, a carbazole group, a fluorenyl group, and a heterocyclic group containing at least one heteroatom selected from among N, O, S and P.
2. The heterocyclic compound of claim 1, wherein Ar3 is any one selected from among the following structures:
Figure US09882146-20180130-C00077
wherein a, c, d and e are each an integer ranging from 1 to 6,
b and b′ are each an integer ranging from 1 to 3,
R1 to R6 are hydrogen,
R′ and R″ are the same or different, and are each independently an unsubstituted alkyl group.
3. The heterocyclic compound of claim 1, wherein Ar1 and Ar2 are the same or different and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group or a substituted or unsubstituted pyridine group,
wherein the term of substituted or unsubstituted means that it is unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group, an aryl group, a carbazole group, a fluorenyl group, and a heterocyclic group containing at least one heteroatom selected from among N, O, S and P.
4. The heterocyclic compound of claim 1, wherein L is a direct bond or a substituted or unsubstituted phenylene group.
5. The heterocyclic compound of claim 1, wherein the compound represented by formula 1 is any one of the following compounds 2-a-1 to 2-a-5, 2-a-8 and 2-a-9:
Figure US09882146-20180130-C00078
Figure US09882146-20180130-C00079
6. The heterocyclic compound of claim 1, wherein the compound represented by formula 1 is any one of the following compounds 2-b-1 to 2-b-5, 2-b-8 and 2-b-9:
Figure US09882146-20180130-C00080
Figure US09882146-20180130-C00081
7. The heterocyclic compound of claim 1, wherein the compound represented by formula 1 is any one of the following compounds 2-c-1 to 2-c-5, 2-c-8 and 2-c-9:
Figure US09882146-20180130-C00082
Figure US09882146-20180130-C00083
Figure US09882146-20180130-C00084
8. The heterocyclic compound of claim 1, wherein the compound represented by formula 1 is any one of the following compounds 2-d-1 to 2-d-5, 2-d-8 and 2-d-9:
Figure US09882146-20180130-C00085
Figure US09882146-20180130-C00086
9. The heterocyclic compound of claim 1, wherein the compound represented by formula 1 is any one of the following compounds 2-e-1, 2-e-2, 2-e-5 and 2-e-6:
Figure US09882146-20180130-C00087
10. An organic electronic device comprising a first electrode, a second electrode and one or more organic material layers interposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprise the heterocyclic compound of claim 1.
11. The organic electronic device of claim 10, wherein the organic electronic device is selected from the group consisting of an organic light-emitting device, an organic solar cell and an organic transistor.
12. The organic electronic device of claim 10, wherein the organic electronic device is an organic light-emitting device comprising the first electrode, the second electrode and one or more organic material layers interposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprise the heterocyclic compound.
13. The organic electronic device of claim 12, wherein the organic material layers include a hole-injecting layer or a hole-transporting layer, which comprises the heterocyclic compound.
14. The organic electronic device of claim 12, wherein the organic material layers include a light-emitting layer comprising the heterocyclic compound as a host.
15. The organic electronic device of claim 12, wherein the organic material layers include an electron-transporting layer comprising the heterocyclic compound.
16. The organic electronic device of claim 12, wherein the organic material layers include, in addition to the organic material layers comprising the heterocyclic compound, a hole-injecting layer or a hole-transporting layer, which comprises an arylamino, carbazole or benzcarbazole group.
17. The organic electronic device of claim 12, wherein the organic material layers comprising the heterocyclic compound comprise the heterocyclic compound as a host, and comprise another organic compound, a metal or a metal compound as a dopant.
18. The organic electronic device of claim 10, wherein the organic electronic device is an organic solar cell comprising the first electrode, the second electrode and one or more organic material layers, including a photoactive layer, interposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprise the heterocyclic compound.
19. The organic electronic device of claim 18, wherein the organic material layers include an electron-transporting layer comprising the heterocyclic compound.
20. The organic electronic device of claim 18, wherein the organic material layers include a photoactive layer comprising the heterocyclic compound.
21. The organic electronic device of claim 18, wherein the organic material layers include an electron donor and an electron acceptor, wherein the electron donor or the electron acceptor comprises the heterocyclic compound.
22. The organic electronic device of claim 10, wherein the organic electronic device is an organic transistor comprising a source, a drain, a gate and one or more organic material layers, wherein one or more of the organic material layers comprise the heterocyclic compound.
23. The organic electronic device of claim 22, wherein the organic material layers include a charge-generating layer comprising the heterocyclic compound.
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